NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1194.68
Volume:	1180.737
LogP:	7.05
LogD:	4.263
LogS:	-4.781
# Rotatable Bonds:	22
TPSA:	333.04
# H-Bond Aceptor:	24
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.049
Synthetic Accessibility Score:	7.938
Fsp3:	0.949
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.297
MDCK Permeability:	0.00018180762708652765
Pgp-inhibitor:	0.982
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.832
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	94.64033508300781%
Volume Distribution (VD):	0.545
Pgp-substrate:	5.095149040222168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.149
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.338
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	1.075
Half-life (T1/2):	0.303

ADMET: Toxicity

hERG Blockers:	0.935
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.798
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.639
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.941
Carcinogencity:	0.062
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.911

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC477319

Natural Product ID:	NPC477319
*Common Name:**	[(2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-[(2S,3S,4R,5R,6S)-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(1S,3R,4S,5R,6R,8R,10S,22S,23S,24S,26R)-4,5,26-trihydroxy-6,24-dimethyl-20-oxo-10-pentyl-2,7,9,21,25-pentaoxatricyclo[20.3.1.03,8]hexacosan-23-yl]oxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxyoxan-3-yl] octanoate
IUPAC Name:	[(2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-[(2S,3S,4R,5R,6S)-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(1S,3R,4S,5R,6R,8R,10S,22S,23S,24S,26R)-4,5,26-trihydroxy-6,24-dimethyl-20-oxo-10-pentyl-2,7,9,21,25-pentaoxatricyclo[20.3.1.03,8]hexacosan-23-yl]oxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxyoxan-3-yl] octanoate
Synonyms:
Standard InCHIKey:	MXBHWGIADFCCGD-HOBAKVMBSA-N
Standard InCHI:	InChI=1S/C59H102O24/c1-10-13-15-19-24-28-37(60)77-47-33(7)73-56(45(68)43(47)66)80-49-35(9)75-59(53(79-54(70)30(4)12-3)52(49)83-55-44(67)41(64)39(62)31(5)71-55)81-48-34(8)74-57-46(69)50(48)78-38(61)29-25-21-18-16-17-20-23-27-36(26-22-14-11-2)76-58-51(82-57)42(65)40(63)32(6)72-58/h30-36,39-53,55-59,62-69H,10-29H2,1-9H3/t30-,31-,32+,33-,34-,35-,36-,39-,40-,41+,42-,43-,44+,45+,46+,47-,48-,49-,50-,51+,52+,53+,55-,56-,57-,58-,59-/m0/s1
SMILES:	CCCCCCCC(=O)O[C@H]1[C@@H](O[C@H]([C@@H]([C@@H]1O)O)O[C@H]2[C@@H](O[C@H]([C@@H]([C@@H]2O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O)O)O)OC(=O)[C@@H](C)CC)O[C@H]4[C@@H](O[C@@H]5[C@@H]([C@@H]4OC(=O)CCCCCCCCC[C@@H](O[C@H]6[C@H](O5)[C@H]([C@H]([C@H](O6)C)O)O)CCCCC)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118716652
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Whole Plant	Dongshan, Nanjing, Jiangsu Province, China	2012-NOV	PMID[25314138]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	9400	nM	PMID[25314138]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	9500	nM	PMID[25314138]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	3700	nM	PMID[25314138]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4100	nM	PMID[25314138]
NPT2	Others	Unspecified		IC50	=	7700	nM	PMID[25314138]
NPT2	Others	Unspecified		IC50	>	10000	nM	PMID[25314138]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC477319 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	651
0.1-0.2	4433
0.2-0.3	13735
0.3-0.4	11449
0.4-0.5	7285
0.5-0.6	2990
0.6-0.7	1549
0.7-0.8	508
0.8-0.85	12
0.85-0.9	8
0.9-0.95	20
0.95-1	57

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC143421
1.0	High Similarity	NPC477317
1.0	High Similarity	NPC259294
1.0	High Similarity	NPC472200
1.0	High Similarity	NPC290012
1.0	High Similarity	NPC119583
1.0	High Similarity	NPC169345
1.0	High Similarity	NPC472203
1.0	High Similarity	NPC472201
1.0	High Similarity	NPC89843
1.0	High Similarity	NPC126685
1.0	High Similarity	NPC27289
1.0	High Similarity	NPC123204
1.0	High Similarity	NPC307400
1.0	High Similarity	NPC477318
1.0	High Similarity	NPC183888
1.0	High Similarity	NPC44782
1.0	High Similarity	NPC477331
1.0	High Similarity	NPC472204
1.0	High Similarity	NPC224953
1.0	High Similarity	NPC472202
1.0	High Similarity	NPC184915
1.0	High Similarity	NPC115013
1.0	High Similarity	NPC472205
0.9867	High Similarity	NPC267592
0.974	High Similarity	NPC60849
0.974	High Similarity	NPC477332
0.974	High Similarity	NPC472352
0.9733	High Similarity	NPC146992
0.9733	High Similarity	NPC477346
0.9733	High Similarity	NPC85759
0.9733	High Similarity	NPC294748
0.9733	High Similarity	NPC22742
0.9733	High Similarity	NPC158302
0.9733	High Similarity	NPC477344
0.96	High Similarity	NPC477320
0.96	High Similarity	NPC113745
0.96	High Similarity	NPC281563
0.96	High Similarity	NPC477328
0.96	High Similarity	NPC477326
0.96	High Similarity	NPC477323
0.96	High Similarity	NPC477325
0.96	High Similarity	NPC477330
0.96	High Similarity	NPC109887
0.96	High Similarity	NPC475425
0.96	High Similarity	NPC477329
0.96	High Similarity	NPC146380
0.9481	High Similarity	NPC297768
0.9481	High Similarity	NPC173328
0.9481	High Similarity	NPC475270
0.9481	High Similarity	NPC475327
0.9481	High Similarity	NPC476087
0.9481	High Similarity	NPC477347
0.9481	High Similarity	NPC475667
0.9481	High Similarity	NPC269318
0.9481	High Similarity	NPC186992
0.9481	High Similarity	NPC238056
0.9333	High Similarity	NPC477350
0.9211	High Similarity	NPC476781
0.9211	High Similarity	NPC476783
0.9211	High Similarity	NPC216883
0.9211	High Similarity	NPC476782
0.8933	High Similarity	NPC225748
0.8933	High Similarity	NPC206823
0.8933	High Similarity	NPC163812
0.8933	High Similarity	NPC39266
0.8933	High Similarity	NPC169085
0.8933	High Similarity	NPC9763
0.8667	High Similarity	NPC52268
0.8667	High Similarity	NPC53760
0.8533	High Similarity	NPC241265
0.8533	High Similarity	NPC211428
0.8533	High Similarity	NPC285003
0.8442	Intermediate Similarity	NPC291228
0.8442	Intermediate Similarity	NPC308096
0.84	Intermediate Similarity	NPC67099
0.84	Intermediate Similarity	NPC250619
0.84	Intermediate Similarity	NPC50228
0.84	Intermediate Similarity	NPC97736
0.8312	Intermediate Similarity	NPC184550
0.8312	Intermediate Similarity	NPC185419
0.8267	Intermediate Similarity	NPC206601
0.8202	Intermediate Similarity	NPC44682
0.8202	Intermediate Similarity	NPC238264
0.8202	Intermediate Similarity	NPC163409
0.8202	Intermediate Similarity	NPC477345
0.8202	Intermediate Similarity	NPC477348
0.8022	Intermediate Similarity	NPC475164
0.8022	Intermediate Similarity	NPC476066
0.8022	Intermediate Similarity	NPC475375
0.8022	Intermediate Similarity	NPC475540
0.8022	Intermediate Similarity	NPC475241
0.8022	Intermediate Similarity	NPC475593
0.8022	Intermediate Similarity	NPC475525
0.8022	Intermediate Similarity	NPC473765
0.8022	Intermediate Similarity	NPC473605
0.8	Intermediate Similarity	NPC471761
0.8	Intermediate Similarity	NPC190418
0.8	Intermediate Similarity	NPC471760
0.8	Intermediate Similarity	NPC76881
0.8	Intermediate Similarity	NPC12040
0.7978	Intermediate Similarity	NPC477349
0.7976	Intermediate Similarity	NPC248415
0.7867	Intermediate Similarity	NPC6848
0.7733	Intermediate Similarity	NPC325773
0.7727	Intermediate Similarity	NPC51662
0.7662	Intermediate Similarity	NPC477756
0.7662	Intermediate Similarity	NPC477764
0.7662	Intermediate Similarity	NPC477752
0.7662	Intermediate Similarity	NPC477751
0.7564	Intermediate Similarity	NPC477754
0.7564	Intermediate Similarity	NPC477761
0.7564	Intermediate Similarity	NPC477759
0.7564	Intermediate Similarity	NPC477758
0.7564	Intermediate Similarity	NPC477760
0.75	Intermediate Similarity	NPC22709
0.7475	Intermediate Similarity	NPC126753
0.7471	Intermediate Similarity	NPC156089
0.7471	Intermediate Similarity	NPC38295
0.7471	Intermediate Similarity	NPC473500
0.7471	Intermediate Similarity	NPC470313
0.7467	Intermediate Similarity	NPC477757
0.7467	Intermediate Similarity	NPC477763
0.7467	Intermediate Similarity	NPC477755
0.7467	Intermediate Similarity	NPC477762
0.7467	Intermediate Similarity	NPC477750
0.7467	Intermediate Similarity	NPC477753
0.7449	Intermediate Similarity	NPC469827
0.7449	Intermediate Similarity	NPC231271
0.7449	Intermediate Similarity	NPC470519
0.7426	Intermediate Similarity	NPC471431
0.7416	Intermediate Similarity	NPC470657
0.74	Intermediate Similarity	NPC207693
0.7333	Intermediate Similarity	NPC31349
0.7333	Intermediate Similarity	NPC314364
0.73	Intermediate Similarity	NPC471430
0.73	Intermediate Similarity	NPC287269
0.7255	Intermediate Similarity	NPC470622
0.7245	Intermediate Similarity	NPC310031
0.7245	Intermediate Similarity	NPC80191
0.7241	Intermediate Similarity	NPC21693
0.7241	Intermediate Similarity	NPC236649
0.7228	Intermediate Similarity	NPC473688
0.7228	Intermediate Similarity	NPC231566
0.7228	Intermediate Similarity	NPC471626
0.7228	Intermediate Similarity	NPC262567
0.7228	Intermediate Similarity	NPC469826
0.7216	Intermediate Similarity	NPC471426
0.7216	Intermediate Similarity	NPC471428
0.7216	Intermediate Similarity	NPC471427
0.72	Intermediate Similarity	NPC273189
0.72	Intermediate Similarity	NPC184805
0.72	Intermediate Similarity	NPC317023
0.7176	Intermediate Similarity	NPC474003
0.7158	Intermediate Similarity	NPC215570
0.7157	Intermediate Similarity	NPC92297
0.7157	Intermediate Similarity	NPC233433
0.7157	Intermediate Similarity	NPC236753
0.7157	Intermediate Similarity	NPC94086
0.7157	Intermediate Similarity	NPC473817
0.7157	Intermediate Similarity	NPC228190
0.7157	Intermediate Similarity	NPC220836
0.7157	Intermediate Similarity	NPC273002
0.7157	Intermediate Similarity	NPC469825
0.7143	Intermediate Similarity	NPC471550
0.7143	Intermediate Similarity	NPC4328
0.7143	Intermediate Similarity	NPC119592
0.7143	Intermediate Similarity	NPC476068
0.7143	Intermediate Similarity	NPC43550
0.7143	Intermediate Similarity	NPC70809
0.7143	Intermediate Similarity	NPC250247
0.7143	Intermediate Similarity	NPC236638
0.7143	Intermediate Similarity	NPC71065
0.7143	Intermediate Similarity	NPC100639
0.7143	Intermediate Similarity	NPC471385
0.7143	Intermediate Similarity	NPC224381
0.7143	Intermediate Similarity	NPC309907
0.7143	Intermediate Similarity	NPC473714
0.7143	Intermediate Similarity	NPC261506
0.7143	Intermediate Similarity	NPC79643
0.7143	Intermediate Similarity	NPC161717
0.7143	Intermediate Similarity	NPC60557
0.7143	Intermediate Similarity	NPC305981
0.7143	Intermediate Similarity	NPC227551
0.7143	Intermediate Similarity	NPC57484
0.7143	Intermediate Similarity	NPC294453
0.7143	Intermediate Similarity	NPC54636
0.7143	Intermediate Similarity	NPC204414
0.7143	Intermediate Similarity	NPC475160
0.7143	Intermediate Similarity	NPC67857
0.7143	Intermediate Similarity	NPC293330
0.7143	Intermediate Similarity	NPC469782
0.7143	Intermediate Similarity	NPC298034
0.7143	Intermediate Similarity	NPC202828
0.7143	Intermediate Similarity	NPC76972
0.7143	Intermediate Similarity	NPC123199
0.7143	Intermediate Similarity	NPC41061
0.7143	Intermediate Similarity	NPC475140
0.7143	Intermediate Similarity	NPC65105
0.7129	Intermediate Similarity	NPC475234

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC477319 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	709
0.1-0.2	4215
0.2-0.3	2884
0.3-0.4	838
0.4-0.5	323
0.5-0.6	120
0.6-0.7	56
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7831	Intermediate Similarity	NPD7329	Approved
0.7467	Intermediate Similarity	NPD6123	Approved
0.6931	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3181	Approved
0.6887	Remote Similarity	NPD8133	Approved
0.6857	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD8083	Approved
0.6733	Remote Similarity	NPD8138	Approved
0.6733	Remote Similarity	NPD8139	Approved
0.6733	Remote Similarity	NPD8082	Approved
0.6733	Remote Similarity	NPD8086	Approved
0.6733	Remote Similarity	NPD8084	Approved
0.6733	Remote Similarity	NPD8085	Approved
0.6707	Remote Similarity	NPD898	Approved
0.6707	Remote Similarity	NPD897	Approved
0.6707	Remote Similarity	NPD896	Approved
0.6699	Remote Similarity	NPD8393	Approved
0.6667	Remote Similarity	NPD7346	Approved
0.6667	Remote Similarity	NPD3730	Approved
0.6667	Remote Similarity	NPD8275	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8276	Approved
0.6667	Remote Similarity	NPD3728	Approved
0.6602	Remote Similarity	NPD8081	Approved
0.6543	Remote Similarity	NPD7909	Approved
0.6533	Remote Similarity	NPD891	Phase 3
0.6533	Remote Similarity	NPD893	Approved
0.6533	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD892	Phase 3
0.6533	Remote Similarity	NPD888	Phase 3
0.6522	Remote Similarity	NPD3669	Approved
0.6522	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD8307	Discontinued
0.6476	Remote Similarity	NPD8140	Approved
0.6471	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.646	Remote Similarity	NPD8516	Approved
0.646	Remote Similarity	NPD8515	Approved
0.646	Remote Similarity	NPD8517	Approved
0.6429	Remote Similarity	NPD8171	Discontinued
0.64	Remote Similarity	NPD2269	Approved
0.6396	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD8306	Approved
0.6355	Remote Similarity	NPD8305	Approved
0.6316	Remote Similarity	NPD8513	Phase 3
0.6304	Remote Similarity	NPD1780	Approved
0.6304	Remote Similarity	NPD1779	Approved
0.6296	Remote Similarity	NPD8087	Discontinued
0.6267	Remote Similarity	NPD905	Approved
0.6267	Remote Similarity	NPD904	Phase 3
0.6262	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7139	Approved
0.625	Remote Similarity	NPD7140	Approved
0.6207	Remote Similarity	NPD8328	Phase 3
0.6104	Remote Similarity	NPD887	Approved
0.6104	Remote Similarity	NPD895	Approved
0.6104	Remote Similarity	NPD889	Approved
0.6104	Remote Similarity	NPD894	Approved
0.6087	Remote Similarity	NPD8347	Approved
0.6087	Remote Similarity	NPD8345	Approved
0.6087	Remote Similarity	NPD8346	Approved
0.6076	Remote Similarity	NPD2267	Suspended
0.6061	Remote Similarity	NPD6698	Approved
0.6061	Remote Similarity	NPD46	Approved
0.6024	Remote Similarity	NPD8961	Approved
0.6019	Remote Similarity	NPD6412	Phase 2
0.5965	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD8301	Approved
0.5943	Remote Similarity	NPD8300	Approved
0.5909	Remote Similarity	NPD6941	Approved
0.5889	Remote Similarity	NPD1810	Approved
0.5889	Remote Similarity	NPD1811	Approved
0.5877	Remote Similarity	NPD6940	Discontinued
0.5867	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7983	Approved
0.5823	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4802	Phase 2
0.5806	Remote Similarity	NPD4238	Approved
0.5802	Remote Similarity	NPD369	Approved
0.5763	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8080	Discontinued
0.5688	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD8377	Approved
0.5678	Remote Similarity	NPD8294	Approved
0.5667	Remote Similarity	NPD7829	Approved
0.5667	Remote Similarity	NPD7830	Approved
0.5656	Remote Similarity	NPD8448	Approved
0.5645	Remote Similarity	NPD8392	Approved
0.5645	Remote Similarity	NPD8391	Approved
0.5645	Remote Similarity	NPD8390	Approved
0.5631	Remote Similarity	NPD1447	Phase 3
0.5631	Remote Similarity	NPD1446	Phase 3
0.563	Remote Similarity	NPD8296	Approved
0.563	Remote Similarity	NPD8380	Approved
0.563	Remote Similarity	NPD8335	Approved
0.563	Remote Similarity	NPD8444	Approved
0.563	Remote Similarity	NPD8379	Approved
0.563	Remote Similarity	NPD8378	Approved
0.562	Remote Similarity	NPD8340	Approved
0.562	Remote Similarity	NPD8299	Approved
0.562	Remote Similarity	NPD8342	Approved
0.562	Remote Similarity	NPD8341	Approved
0.5619	Remote Similarity	NPD6428	Approved
0.561	Remote Similarity	NPD8959	Approved
0.56	Remote Similarity	NPD8998	Phase 2
0.56	Remote Similarity	NPD8999	Phase 3
0.56	Remote Similarity	NPD8997	Approved
0.56	Remote Similarity	NPD8993	Phase 1
0.56	Remote Similarity	NPD9000	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data